(1'R,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole | 172329-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1'R,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole
• 英文别名: tert-butyl N-[(1R,2S)-1-[tert-butyl(dimethyl)silyl]oxy-3-phenyl-1-(1,3-thiazol-2-yl)propan-2-yl]carbamate
• CAS: 172329-47-4
• 化学式: C₂₃H₃₆N₂O₃SSi
• 分子量: 448.702
• InChiKey: CJSOMRIDLIUSMW-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'R,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole 在 sodium tetrahydroborate 、 4 A molecular sieve 、 四丁基氟化铵 、 copper(II) oxide 、 copper dichloride 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 48.92h， 生成 tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate
  参考文献：
  名称：

  Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV-1 Aspartic Protease

  摘要：

  A new synthesis of hydroxyethylene dipeptide isosteres for Leu-Leu and Phe-Phe in their gamma-lactone form 1a and 1b employing beta-amino-alpha-hydroxy aldehydes with singly and doubly protected nitrogen has been developed. These key intermediates, which are available through the thiazole-aldehyde synthesis from L-leucine and L-phenylalanine, were converted to alkanoates by Wittig olefination and reduction of the ethylenic double bond. Lactonization and stereoselective alkylation at C-2 of the resulting lactones completed the building up of the structural framework. Overall yields were in the range 16-19% for 1a and 22-23% for 1b.

  DOI：

  10.1021/jo00129a037
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (S)-2(tert-butoxycarbonyl)amino-3-phenyl-(R)-1-(2-thiazolyl)propan-1-ol 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以76%的产率得到(1'R,2'S)-2-<2'--1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole
  参考文献：
  名称：

  Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV-1 Aspartic Protease

  摘要：

  A new synthesis of hydroxyethylene dipeptide isosteres for Leu-Leu and Phe-Phe in their gamma-lactone form 1a and 1b employing beta-amino-alpha-hydroxy aldehydes with singly and doubly protected nitrogen has been developed. These key intermediates, which are available through the thiazole-aldehyde synthesis from L-leucine and L-phenylalanine, were converted to alkanoates by Wittig olefination and reduction of the ethylenic double bond. Lactonization and stereoselective alkylation at C-2 of the resulting lactones completed the building up of the structural framework. Overall yields were in the range 16-19% for 1a and 22-23% for 1b.

  DOI：

  10.1021/jo00129a037

文献信息

• Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isostere Inhibitors of Renin and HIV-1 Aspartic Protease
  作者：Alessandro Dondoni、Daniela Perrone、M. Teresa Semola

  DOI：10.1021/jo00129a037

  日期：1995.12

  A new synthesis of hydroxyethylene dipeptide isosteres for Leu-Leu and Phe-Phe in their gamma-lactone form 1a and 1b employing beta-amino-alpha-hydroxy aldehydes with singly and doubly protected nitrogen has been developed. These key intermediates, which are available through the thiazole-aldehyde synthesis from L-leucine and L-phenylalanine, were converted to alkanoates by Wittig olefination and reduction of the ethylenic double bond. Lactonization and stereoselective alkylation at C-2 of the resulting lactones completed the building up of the structural framework. Overall yields were in the range 16-19% for 1a and 22-23% for 1b.